Wikipedia preview

出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/04/05 10:32:21」(JST)

wiki en

Structural formula of the mesylate anion

Ball-and-stick model of the mesylate anion

In chemistry, a mesylate is any salt or ester of methanesulfonic acid (CH₃SO₃H). In salts, the mesylate is present as the CH₃SO₃⁻ anion. When modifying the International Nonproprietary Name of a pharmaceutical substance containing the group or anion, the correct spelling is mesilate (as in imatinib mesilate, the mesylate salt of imatinib).^[1]

Mesylate esters are a group of organic compounds that share a common functional group with the general structure CH₃SO₂O–R, abbreviated MsO–R, where R is an organic substituent. Mesylate is considered a leaving group in nucleophilic substitution reactions.

Preparation

Mesylates are generally prepared by treating an alcohol and methanesulfonyl chloride in the presence of a base, such as triethylamine.^[2]

Mesyl

Related to mesylate, is the mesyl, an abbreviation for methanesulfonyl or CH₃SO₂ (Ms) functional group. For example, methanesulfonyl chloride is often referred to as mesyl chloride. Whereas mesylates are often hydrolytically labile, mesyl groups, when attached to nitrogen are robust with respect to hydrolysis.^[3] This functional group appears in a variety of medications, particularly cardiac (i.e. “antiarrhythmic”) but as sulfonamide moiety. Examples include Sotalol, ibutilide, sematilide, Dronedarone, Dofetilide, E-4031, and Bitopertin .

References

^ World Health Organization (February 2006). "International Nonproprietary Names Modified". INN Working Document 05.167/3. WHO. Retrieved 5 December 2008.
^ Rick L. Danheiser, Yeun-Min Tsai, and David M. Fink (1966). "A General Method for the Synthesis of Allenylsilanes: 1-Methyl-1-(trimethylsilyl)allene". Org. Synth. doi:10.15227/orgsyn.066.0001. (a procedure illustrating the use of mesylates).
^ Valerie Vaillancourt, Michele M. Cudahy, Matthew M. Kreilein and Danielle L. Jacobs "Methanesulfonyl Chloride" in E-EROS Encyclopedia for Reagents in Organic Synthesis. doi:10.1002/047084289X.rm070.pub2

UpToDate Contents

全文を閲覧するには購読必要です。 To read the full text you will need to subscribe.

1. 好酸球増加症候群の治療 treatment of the hypereosinophilic syndromes
2. クローン病の内科的マネージメントにおける試験研究治療 investigational therapies in the medical management of crohn disease
3. 脳卒中の内科的合併症 medical complications of stroke
4. 真性多血症の予後および治療 prognosis and treatment of polycythemia vera
5. 慢性骨髄性白血病の治療のためのインターフェロンα interferon alpha for the treatment of chronic myeloid leukemia

English Journal

Managing progressive disease in patients with GIST: Factors to consider besides acquired secondary tyrosine kinase inhibitor resistance.

Patel S.SourceDepartment of Sarcoma Medical Oncology, The University of Texas, MD Anderson Cancer Center, 1515 Holcombe Blvd, Houston, TX 77030, USA.
Cancer treatment reviews.Cancer Treat Rev.2012 Aug;38(5):467-72. Epub 2011 Oct 27.
The use of tyrosine kinase inhibitors (TKIs) has revolutionized the treatment of patients with unresectable and/or metastatic gastrointestinal stromal tumors (GIST). Currently, imatinib mesylate is the standard first-line treatment for unresectable and/or metastatic GIST, extending recurrence-free a
PMID 22035971

Superparamagnetic surface molecularly imprinted nanoparticles for water-soluble pefloxacin mesylate prepared via surface initiated atom transfer radical polymerization and its application in egg sample analysis.

Liu Y, Huang Y, Liu J, Wang W, Liu G, Zhao R.SourceBeijing National Laboratory for Molecular Sciences, CAS Key Lab of Analytical Chemistry for Living Biosystems, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China.
Journal of chromatography. A.J Chromatogr A.2012 Jul 13;1246:15-21. Epub 2012 Jan 25.
The novel superparamagnetic surface molecularly imprinted Fe(3)O(4)@MIP nanoparticles for water-soluble pefloxacin mesylate (PEF-M) were prepared via surface initiated atom transfer radical polymerization (si-ATRP). The binary mixture of methanol and water was selected as the polar solvents for fabr
PMID 22321951

Japanese Journal

臨床報告メシル酸イマチニブによる術前化学療法にて完全奏効を得た胃GISTの1例

村上裕樹,尾崎知博,齊藤博昭 [他]
臨床外科 = Journal of clinical surgery 70(6), 781-785, 2015-06
NAID 40020487052

腹腔内出血をきたした胃GISTの破裂の1例

柴田健一,蜂谷修,鈴木武文,川村一郎,高須直樹,木村理
山形大学紀要. 医学 : 山形医学 33(1), 23-28, 2015-02-15
消化管間質腫瘍(Gastrointestinal stromal tumor,以下GIST)は、壁外性に発育し、破裂により腹腔内出血を来すことがある。今回、われわれは、胃GISTの破裂により腹腔内出血をきたした1例を経験したので、報告する。症例は45歳の女性。2013年7月の上旬より上腹部痛を自覚した。次第に痛みが増強し、その翌日に当院の救急外来を受診した。腹部造影CTで胃体部から壁外性に発 …
NAID 110009889044

Imatinib mesylate treatment in a dog with gastrointestinal stromal tumors with a c-kit mutation

IRIE Mitsuhiro,TAKEUCHI Yoshinori,OHTAKE Yuzo,SUZUKI Hitomi,NAGATA Nao,MIYOSHI Takuma,KAGAWA Yumiko,YAMAGAMI Tetsushi
Journal of Veterinary Medical Science advpub(0), 2015
… Upon detection of the recurrent tumors, we initiated treatment with imatinib mesylate (10 mg/kg, q 24 hr). …
NAID 130005075568

Related Pictures

★リンクテーブル★

リンク元	「メシル酸塩」「methanesulfonate」「mesilate」「メシル酸」「メシレート」
拡張検索	「deferoxamine mesylate」「dihydroergocryptine mesylate」「fenoldopam mesylate」